合成梨圆蚧性信息素主要组分的简易路线

A simple route for the synthesis of the main component of San Jose Scale's sex pheromone

乙酰乙酸乙酯与1-溴-3-甲基-3-丁烯进行烷基化、皂化脱羧反应得6-甲基-6-庚烯-2-酮3。酮3与氯化(β-羟乙基)三苯基鏻在碱 NaH/DMSO 和 NaoEt/EtOH 作用下进行 Schlosser-Wittig 反应,然后酯化,得3,7-二甲基-2,7-辛二烯-1-醇丙酸酯1,即梨圆蚧性信息素的主要组分。总产率23.8%。产物中1a/1b=19/81。

6-Methyl-6-hepten-2-one 3 was obtained by the alkylation of acetoacetic ester with 1bromo-3-methyl-3-butene followed by saponifi-cation and decarboxylation of the alkylate.Thisketone 3 was made to undergo Schlosser-Wittigreaction with phosphonocholine chloride usingsodium hydride in DMSO and sodium ethoxidein EtOH as base-solvent combinations,then byesterification,3,7-dimethyl-2,7-octadien-1-ylpropanoate 1,the main component of San JoesScale's sex pheromone was obtained.The overallyield was 23.8%.The product contained the Zand E isomers in a ratio of 19% to 81%.